The article is timed to the three anniversaries of the prominent statesmen of the Imperial Russia, Peter the Great (the 350th anniversary of his birth), P.A. Stolypin (the 160th anniversary of his birth) and M.M. Speransky (the 250th anniversary of his birth) in 2022. The author highlights general and special features in their activities and the context of their reforms. Common features include the undoubtedly modernizing nature of the initiatives of all three reformers, as well as the lack or obvious inadequacy of the social environment, which could support the reforms being implemented or planned. Peter the Great overcame this obstacle, firstly, with the help of his power resources, and secondly, by the radicalism of changes. In many respects this is the source of the ambivalence of his reforms. On the one hand, modernization of Russia was in line with what was happening at the same time in other European countries. On the other hand, Peter’s modernization led to strengthening of the archaic features of the autocracy. However, for Peter, the lack of social support was not a fatal insurmountable circumstance. Moreover, such a support was eventually formed as a result of his reforms. An altogether different fate was in store for the initiatives of Stolypin and Speransky. Support from the supreme power for both was inconsistent, and the political subjectivity of the potential recipient of the reforms was clearly insufficient or non-existent, which prevented them from implementing their plans. What was special about the changes carried out or at least simply conceived by Peter, Stolypin, and Speransky was the very context of these persons’ eras and thus the degree of maturity of both the social base of reforms and society as a whole for modernizing transformations. Special attention in the article is paid to Speransky’s projects. It examines their content and personality of the reformer. The author argues that reforms in Russia were often conditioned not by the level of socio-economic development but by political considerations.